Shelter Island Holidays from £1,557
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Your Shelter Island Holiday
Lock in a Shelter Island holiday package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighbourhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organising a tailored Shelter Island holiday is a cinch with Expedia.
Top Shelter Island Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The High Line Hotel
Manhattan
£1,565
per person
21 Nov - 28 Nov
found 14 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,003 reviews)
There are hotels that have "shabby chic" and there are hotels that, like this one, are just neglectfully shabby. What a disappointment for the amount of money spent on the room... that there is no real lobby is a structural choice they made, which is sad. That they refuse to turn the coffee station into a bar at night (when the outdoor bar is closed due to weather) is a poor choice, like they don't care about the guests... that they leave a window air-condition in the window when it's cold and have a tape keep the plastic together--and the outside noise and cold air come into the first-floor room, is a choice, as well. The curtains could use rehanging, the towels are so frayed that they tear, and despite claiming it's a "deluxe" room, there is neither light not end-table on one side (and you have to jump over the bed to get to your side of the bed (when coupled).
Reviewed on 27 Sept 2026
LGA AIRPORT
Queens
£3,141
per person
21 Dec - 28 Dec
found 1 day ago
Return direct flight included
London (LHR) to New York (JFK)
10/10 Exceptional! (2 reviews)
The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future.
Reviewed on 24 Dec 2025
Where to stay in Shelter Island
Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Silver Beach
While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.
Coecles Harbor
While Coecles Harbor isn't home to many top sights, Gardiner's Bay Country Club and Mashomack Preserve are some notable places to visit nearby.
Menantic Creek
While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Wades Beach and Shelter Island Historical Society.
Hay Beach
When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.
Shorewood
While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wades Beach and Shell Beach.
Shelter Island Beach Holiday
There's nothing that can beat a Shelter Island holiday. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favourite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 1 mile from downtown. However, you'll also discover a fantastic range of Shelter Island holiday deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.
Shelter Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,350 |
Max Temp Winter | 4ºC |
Max Temp Summer | 24ºC |
Top Sights | East Hampton Main Beach, Wolffer Estates Vineyard and 67 Steps Beach |
Top hotels in Shelter Island
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
£68
12 Oct - 13 Oct
includes taxes & fees
8/10 Very good! (1,002 reviews)
"Nice place !"
Reviewed on 1 Oct 2026
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
£384
3 Nov - 4 Nov
includes taxes & fees
Offshore Montauk
71 S Emerson Ave Montauk NY
£190
2 Nov - 3 Nov
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Shelter Island attractions
Shell Beach
10.0/10 (1 review)
This peaceful shoreline offers a tranquil escape with abundant shells and wildflowers framing its natural beauty. Enjoy both calm harbour waters and more dynamic waves, perfect for beachcombing and wildlife spotting.
Wades Beach
10.0/10 (1 review)
Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
Mashomack Preserve
Explore 2,039 acres of pristine wilderness across diverse ecosystems at Mashomack Preserve. The 20+ miles of trails offer intimate encounters with over 200 bird species in tidal creeks, oak forests, and marshes.
Gardiner's Bay Country Club
This historic 1896 golf club showcases rolling fairways with stunning views of Gardiner's Bay and Coecles Harbour. Members enjoy challenging play on the Seth Raynor-influenced course and refined dining in the clubhouse.
Shelter Island Historical Society
8.0/10 (1 review)
This historic museum preserves Shelter Island's maritime heritage through artefacts and photographs. Explore special exhibits or attend seasonal events celebrating local culture.
Menhadden Lane Beach
8.8/10 (3 reviews)
This tranquil beach on Shelter Island's east side offers serene views of Gardiner's Bay and the 'Bug' Lighthouse. Bring a blanket, find a quiet spot, and watch sailboats glide across the pristine waters.
Havens House
Built in 1743, Havens House served as a store, tavern, school, and post office before becoming the Shelter Island Historical Society. Explore its wide plank floors and exhibits showcasing the island's unique heritage.
Frequently asked questions
How much does a Shelter Island travel package cost?
Starting from just £1,557, a travel package is your ticket to affordable travel. Customize your Shelter Island trip by choosing from our great range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Shelter Island travel package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or alter your Shelter Island travel package at no cost within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, hotel or airline may impose a charge. Need more information? Have a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Shelter Island?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Pick and choose a combination that suits you and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 properties globally, which lets you customize your Shelter Island holiday.
Does Expedia offer Book Now, Pay Later Shelter Island holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your budget. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Browse these flexible payment options:
- Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying small amounts each month sounds right for you, pick this option during the checkout process.
- Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
- Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.
What are the top hotels in Shelter Island?
People heading to Shelter Island often book a room at Waterfront House With Dock And Private Beach or Lovely Shelter Island Cottage With Panoramic Bay Views. You'll find them in Silver Beach. Another happening neighbourhood is Hay Beach. Waterfront House With Dock And Private Beach and Tranquil Resort Style Retreat With Luxury Gunite Pool 2 Min From Sandy Beaches are reputable choices in this part of town.
How far in advance should I book my Shelter Island holiday?
While prices do change, we generally suggest booking your spot as soon as possible. Many international airfares are available on Expedia up to a year in advance. If circumstances have left you booking last minute, you might still be in luck. Cheap tickets to Shelter Island sometimes appear just weeks before departure.
What does an Expedia Shelter Island travel package include?
From flights and hotels to rental cars, Expedia can help you put together a Shelter Island package that's right for you. Holidaying for a while? Consider a hotel, flight and rental car bundle. If your break is short, a hotel and airfare deal could suit you better. Activities can also be added once you've made your booking. Our packages make it easy to plan and save.
What should I know before booking a Shelter Island travel package?
Whether it's adventure or relaxation you're craving, a Shelter Island travel package lets you organise your escape your way. Plus, you'll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Shelter Island Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our travel packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
